In this paper the authors examine the perceptions of mothers about the schooling transitions, including transitions to postschool options, made by their adult child with an intellectual disability (ID). Twenty mothers of an adult child with an ID living in New South Wales, Australia, and the Czech Republic, aged 48 years or older, were recruited to participate in this study. Mothers were interviewed following a semistructured protocol. The audiotaped interviews were transcribed verbatim, and analysed using a constant comparison analytic approach. The experiences and issues faced by mothers at differing transitions of their adult child with an ID will be discussed, including issues of school selection, lifelong planning, and engaging with professionals. Common and unique themes within and between each country will be drawn, along with a comparison of findings from recent research reporting on transition experiences of mothers with young children with ID. The concluding discussion will focus on lessons learned about lifelong transition experiences, and pose future directions for enhancing the quality of transitions for persons with special needs and their families.